Biodegradation and bioaccumulation of fenitrothion in rat liver

Roy, Shalini; Roy, Sharmila; Kumar, Reena; Sharma, C.B.; Pereira, Ben. J.

doi:10.1002/bmc.318

Cited by 11 publications

(5 citation statements)

References 17 publications

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“…22,23,36 Cytochrome P450 was considered to be responsible for those metabolisms (phase I metabolism). 21,45 The two major degradation pathways of FNT by C. elegans in the current study were also found in other animals, such as rats, 46 female goats, 47 and birds. 48 Furthermore, aromatic hydroxylation during the metabolism of FNT in birds, 48 which has not reported in plants and soil, was also detected in C. elegans.…”

Section: Journal Of Agricultural and Food Chemistrysupporting

confidence: 78%

“…elegans can metabolize a wide variety of xenobiotics as those reported in human and animal studies through N-oxidation and N-deethylation, , demethylation, and hydroxylation. ,, Cytochrome P450 was considered to be responsible for those metabolisms (phase I metabolism). , The two major degradation pathways of FNT by C. elegans in the current study were also found in other animals, such as rats, female goats, and birds . Furthermore, aromatic hydroxylation during the metabolism of FNT in birds, which has not reported in plants and soil, was also detected in C.…”

Section: Resultssupporting

confidence: 48%

See 1 more Smart Citation

Metabolism of an Insecticide Fenitrothion by Cunninghamella elegans ATCC36112

Zhu

Jeong

et al. 2017

J. Agric. Food Chem.

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In this study, the detailed metabolic pathways of fenitrothion (FNT), an organophosphorus insecticide by Cunninghamella elegans, were investigated. Approximately 81% of FNT was degraded within 5 days after treatment with concomitant accumulation of four metabolites (M1-M4). The four metabolites were separated by high-performance liquid chromatography, and their structures were identified by mass spectroscopy and/or nuclear magnetic resonance. M3 is confirmed to be an initial precursor of others and identified as fenitrothion-oxon. On the basis of their metabolic profiling, the possible metabolic pathways involved in phase I and II metabolism of FNT by C. elegans was proposed. We also found that C. elegans was able to efficiently and rapidly degrade other organophosphorus pesticides (OPs). Thus, these results will provide insight into understanding of the fungal degradation of FNT and the potential application for bioremediation of OPs. Furthermore, the ability of C. elegans to mimic mammalian metabolism would help us elucidate the metabolic fates of organic compounds occurring in mammalian liver cells and evaluate their toxicity and potential adverse effects.

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Section: Journal Of Agricultural and Food Chemistrysupporting

confidence: 78%

Section: Resultssupporting

confidence: 48%

Metabolism of an Insecticide Fenitrothion by Cunninghamella elegans ATCC36112

Zhu

Jeong

et al. 2017

J. Agric. Food Chem.

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“…Cytochrome P-450 enzymes may be implicated in both the hydroxylation and reduction reactions of MNP; however a combination of peroxidase and oxidase activities may be responsible for the condensation reaction. Recently, the reduction product 4-amino-3-methylphenol was found to be a major metabolite of fenitrothion metabolism in rat liver in vivo; however condensation products were not reported (28).…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of 3-Methyl-4-nitrophenol, a Main Product of the Insecticide Fenitrothion, by Aspergillus niger

Kanaly

Kim

Hur

2005

J. Agric. Food Chem.

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Biotransformation of the environmental pollutant 3-methyl-4-nitrophenol (MNP), a newly characterized estrogenic chemical, and the primary breakdown product of the heavily used insecticide fenitrothion was investigated using a common soil fungus. In 96 h, daily culture sacrifice, extraction, and analysis showed that the filamentous fungus, Aspergillus niger VKM F-1119, removed more than 85% of the MNP present in solution (original concentration = 25 mg/L), mostly through biodegradation. Additionally, in 16-day time-course studies, A. niger was capable of biotransformation of MNP at concentrations as high as 70 mg/L. Gas chromatography mass spectroscopy (MS) analyses of culture fluid extracts indicated the formation of four metabolites: 2-methyl-1,4-benzenediol, 4-amino-3-methylphenol, and two singly hydroxylated derivatives of MNP. Culture scale up and metabolite analysis by liquid chromatography MS resulted in the confirmation of the original metabolites plus the detection of an azo derivative metabolite that has not been previously reported before during MNP biodegradation by any micro-organisms.

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“…The pattern of distribution and elimination of fenitrothion in male and female rats was similar regardless of receiving a single nontoxic dose (15 mg/kg) exposure, a single toxic dose (105 mg/kg) exposure, or repeated nontoxic dose exposure (15 mg/kg every other day five times, and then treated with 15 mg/kg fenitrothion) (392,401) (405).…”

Section: Experimental Studiesmentioning

confidence: 99%

Organophosphorus Pesticides

Storm¹

2012

Patty's Toxicology

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Most organophosphorus compounds today fall into two general groups: the so‐called nerve agents, that are very acutely toxic and organophosphorus pesticides that are less toxic. Nerve agents were generally the first toxic organophosphorus developed, and were the original basis for organophosphorus pesticides. Interest about nerve agents has increased lately given concerns about their potential use in terrorist acts. Organophosphate nerve agents and pesticides are a highly diverse group of chemicals. They are all characterized by their ability to inhibit the enzyme acetylcholinesterase (AChE) that deactivates the neurotransmitter acetylcholine (ACh). At present, the widest use of organophosphorus compounds is as pesticides, although they have also been used as therapeutic agents, gasoline additives, hydraulic fluids, cotton defoliants, fire retardants, plastic components, growth regulators, and industrial intermediates to a much smaller extent. Compounds in this class are numerous and have been categorized in many ways according to the nature of the substituents. Gallo and Lawryk (1991) [2], for example, categorized them into four main groups I–IV based on the characteristics of the leaving group (X). Group I compounds, phosphorylcholines, have a leaving group that contains a quaternary nitrogen and are among the most potent organophosphates (e.g., Shradan). Group II compounds, fluorophosphates, have a fluoride leaving group and are also generally highly toxic (e.g., diisopropyl fluorophosphate). Group III compounds have leaving groups that contain cyanide or a halogen other than fluoride and are generally less potent than group I or II (e.g., Parathion). Group IV contains most of the organophosphates used as insecticides today. These compounds have alkoxy, alkylthio, aryloxy, arylthio, or heterocyclic leaving groups and a wide variety of other substituents. Another classification scheme is based on the nature of the atoms that immediately surround the central phosphorus atom and results in 14 different categories. According to this scheme, phosphates are the prototype for the entire class and are those compounds where all four atoms that surround the phosphorus atom are oxygen (e.g., dichlorvos, mevinphos). Sulfur‐containing organophosphate compounds (phosphorothioates, phosphorothiolates, phosphorodithioates, and phosphorodithiolates) are far more numerous than phosphates and include well‐recognized organophosphate insecticides such as parathion, diazinon, chlorpyrifos, etc. Other groups contain nitrogen (phosphoramides and phosphorodiamides), nitrogen and sulfur (phosphoramidothionates and phosphoramidothiolates), carbon (phosphonates and phosphinates), or carbon and sulfur (phosphonothionates, phosphonothionothiolates, and phosphinothionates). All aspects of organophosphate chemistry, toxicity, analysis, and exposure potential have been previously and comprehensively reviewed. In addition, information regarding the toxicity of organophosphorus pesticides in particular has expanded greatly in recent years as a result of toxicity data supplied by registrants to the U.S. EPA's Office of Pesticides to support reregistration. These data have been made publicly available by the U.S. EPA on its Internet Web site ( www.epa.gov/pesticides ). The following discussion draws heavily from recent reviews and also includes summaries of relevant toxicity data submitted to, and made available by, the U.S. EPA.

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Biodegradation and bioaccumulation of fenitrothion in rat liver

Cited by 11 publications

References 17 publications

Metabolism of an Insecticide Fenitrothion by Cunninghamella elegans ATCC36112

Metabolism of an Insecticide Fenitrothion by Cunninghamella elegans ATCC36112

Biotransformation of 3-Methyl-4-nitrophenol, a Main Product of the Insecticide Fenitrothion, by Aspergillus niger

Organophosphorus Pesticides

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